1. Field of the Invention
This invention relates to novel 3-(vinylpyridinium)-2-hydroxypropyl alkyl ether salts.
2. Description of the Prior Art
Quaternary ammonium monomers derived from acrylamide or methacrylamide are revealed in U.S. Pat. No. 4,212,820. The monomers, homopolymers, or interpolymers of these compounds may be used as additives in a number of processes or employed per se to produce a variety of manufactured articles.
The variety of monomers that can be produced is often limited by the competing uncontrollable polymerization reaction. In industrial practice it is typically necessary to produce a stable monomer which may later be subjected to a controlled polymerization process. Monomers which exist only fleetingly in an uncontrollable polymerization are of no use in a practical sense because they cannot be synthesized into useful products.
Converting vinyl pyridine monomers to their quaternary ammonium compounds is of considerable interest but heretofore has not been appreciably applied in the useful arts. The literature is replete with examples indicating spontaneous polymerization of vinyl pyridine occurring in polar solvent media under the influence of acid or alkylating reagents. Spontaneous, uncontrolled polymerization of vinyl pyridine monomers is mentioned in the following references:
1. V. A. Kabanov and V. A. Pelrovskaya Vysokomol. Soedin. BIO, 797(1968) PA0 2. O. V. Kargina, M. V. Vlganovo, V. A. Kabanov and V. A. Kargin, Vyosokomol. Soedin., A9, 340(1967) PA0 3. V. A. Kargin, V. A. Karbanov, K. F. Aliev and E. F. Rozvodovskii, Dokl. Akad. Nauk SSSR, 160, 604(1965) PA0 4. I. Iwatsu, T. Kobubee, K. Motomatsu, M. Tsugi and Y. Yamashita, Makromol. Chem., 120, 154(1968) PA0 5. I. Miehke and H. Ringsorf, J. Polymer Sci., Pt., C, 31,107 (1970); Polymer Letters 9, 1 (1971); Makromol. Chem., 142, 319 (1971) PA0 6. J. L. Salamone, B. Snider, and W. L. Fitch, Polymer Letters 9, 13 (1971); J. Polymer Sci., P A1, 9 1493 (1971)
The reference Functional Monomers, Volume 2, by R. H. Nocum & E. B. Nyquist, Marcel Dekker Inc., N.Y. (1974) establishes that (1) successful alkylation of vinyl pyridine to a quaternary ammonium monomer is unexpected (p. 632); (2) polymers containing the pyridinium moiety were made by alkylation of polymer containing pyridine (p. 629), and (3) polymers containing the pyridinium quaternary ammonium group are useful (p. 648).
It is the object of the present invention to prepare a new class of stable surface active quaternary pyridinium monomer which can be later controllably polymerized into a variety of useful products such as surfactants, flocculants and coagulants.